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  • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
  • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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  • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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  • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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  • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
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  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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  • C10M2219/088—Neutral salts
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  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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  • C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
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  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• This invention relates to lubricating oil compositions containing an ashless detergent.
• crankcase lubricating oil compositions comprise a mineral or synthetic lubricating oil and a quaternary ammonium salt wherein the cation is derived from the reaction product of a tertiary amine with an olefin oxide and water.
• the quaternary ammonium salts can be made in two stages:
• quaternary ammonium hydroxide is neutralised with an organic acid to form a quaternary ammonium salt, i.e. ##EQU2##
• tertiary amines which are suitable include
• R 1 , R 2 and R 3 which may be the same or different are alkyl, cycloalkyl, alkenyl, cycloalkenyl, substituted alkyl and alkenyl groups or aromatic and substituted aromatic groups.
• R 1 , R 2 and R 3 preferably have 1 to 20 carbon atoms.
• Examples of this type of amine are trimethyl amine, ethyl dimethylamine, n-propyldimethylamine, triethanolamine, N,N dimethyl benzyl amine, N,N dimethyl cyclohexylamine and N,N dimetylaniline.
• R 14 is the same as R 4 above.
• R 16 , R 17 , R 18 , and R 19 which may be the same or different, are hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aromatic or substituted aromatic group.
• R 16 , R 17 , R 18 , and R 19 which may be the same or different, are hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aromatic or substituted aromatic group.
• Specific examples are ethylene oxide, propylene oxide, but-1-ene oxide, but-2-ene oxide, oct-1-ene oxide and styrene oxide.
• the organic acid which is used in the second stage of the reaction include carboxylic acids, carboxylic acid anhydrides, dialkyldithiophosphoric acids, diaryldithiophosphoric acids, phenols, sulphurised phenols, sulphonic acids and the acids and the anhydrides resulting from the reacton of an olefin with phosphorus sulphides.
• the carboxylic acids include:
• R is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aromatic or substituted aromatic group.
• acids include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, palmitic acid, stearic acid, cyclohexanecarboxylic acid, 2-methylcyclohexanecarboxylic acid, 4-methylcyclohexane carboxylic acid, oleic acid, linoleic acid, linolenic, cyclohex-2-eneoic acid, benzoic acid, 2-methylbenzoic acid, 3-methylbenzoic acid, 4-methylbenzoic acid, salicylic acid, 2-hydroxy-4-methylbenzoic acid, 2-hydroxy-4-ethylsalicylic acid, p-hydroxybenzoic acid, 3,5,-di-ti-butyl-4-hydroxybenzoic acid, o-aminobenzoic acid, p-aminobenzoic acid,
• n is zero or an integer -- including oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid etc. Also included are acids of of the type: ##EQU9## where x is zero or an integer, y is zero or an integer and x and y may or may not be equal and R is defined as in (i).
• acids examples include the alkyl or alkenyl succinic acids, 2-metylbutane dioic acid, 2-ethylpentanedioic acid, 2-n-dodecylbutanedioic acid, 2-n-dodecenylbutanedioic acid, 2-phenylbutanedioic acid, 2-(p-methylphenyl) butanedioic acid.
• polysubstituted alkyl dicarboxylic acids wherein other R groups as described above may be substituted on the alkyl chain. These other groups may be substituted on the same carbon atom or different atoms.
• Such examples include 2,2-dimethylbutanedioic acid; 2,3-dimethylbutanedioic acid; 2,3,4 trimethylpentanedioic acid; 2,2,3-trimethylpentanedioic acid; 2-ethyl-3-methylbutanedioic acid etc.
• the dicarboxylic acids also include acids of the type
• n is an integer.
• examples include maleic acid, fumaric acid, pent-2-enedioic acid, hex-2-enedioic acid; hex-3-endioic acid; 5-methylhex-2-enedioic acid; 2,3-dimethylpent-2-enedioic acid; 2-methylbut-2-enedioic acid, 2-dodecylbut-2-enedioic acid; 2-polyisobutylbut-2-enedioic acid etc.
• the dicarboxylic acids also include aromatic dicarboxylic acids e.g. phthalic acid, isophthalic acid, terephthalic acid and substituted phthalic acids of general type: ##SPC1##
• aromatic dicarboxylic acids e.g. phthalic acid, isophthalic acid, terephthalic acid and substituted phthalic acids of general type: ##SPC1##
• R as defined (i) and n 1,2,3, or 4 but when n> 1 then the two R groups may be similar or different.
• examples of such acids include 3-methylbenzene-1,2,-dicarboxylic acid; 4-phenylbenzene-1,3-dicarboxylic acid; 2-(1-propenyl) benzene-1,4-dicarboxylic acid; 3,4-dimethylbenzene-1,2-dicarboxylic acid etc.
• the carboxylic acid anhydrides include the anhydrides that may be derived from the carboxylic acids described above. Also included are the anhydrides that may be derived from a mixture of any of the carboxylic acids described above. Specific examples include acetic anhydride, propionic anhydride, benzoic anhydride, maleic anhydride, succinic anhydride, didecylsuccinic anhydride, dodecenylsuccinic anhydride, polyisobutylenesuccinic anhydride, phthalic anhydride, 4-methylphthalic anhydride.
• dialkyldithiophosphoric acids and diaryldithiophosphoric acids include products of the formula: ##EQU10## where R is an alkyl, cycloalkyl, alkenyl or cycloalkenyl group and Ar is an aromatic or substituted aromatic group.
• R is an alkyl, cycloalkyl, alkenyl or cycloalkenyl group and Ar is an aromatic or substituted aromatic group.
• the total number of carbon atoms in the R or Ar group may be from 1-80 but the preferred number is 4-20.
• the acids which may be made by the reaction of any alcohol or phenol with phosphorus pentasulphide include as specific examples: dimethyldithiophosphoric acid; diethyldithiophosphoric acid, di-n-propyldithiophosphoric acid; di-n-butyldithiophosphoric acid; di-sec-butyldithiophosphoric acid, di-iso-butyldithiophosphoric acid; di-t-butyldithiophosphoric acid, diphenyldithiophosphoric acid; di(p-methylphenyl) dithiophosphoric acid; di (o-methylphenyl)dithiophosphoric acid; di(p-nonylphenyl) dithiophosphoric acid; di(p-dodecylphenyl) dithiophosphoric acid etc.
• phenols from which the anion of the quaternary ammonium result may be derived are of many different types.
• suitable phenols include:
• n 1,2,3,4 or 5
• R is defined below and when n ⁇ 1 then the substituents may be the same or different.
• R may be hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aromatic or substituted aromatic.
• the hydrocarbon group(s) may be bonded to the benzene ring by a keto or thio-keto group.
• the hydrocarbon group(s) may be bonded through an oxygen sulphur or nitrogen atom.
• phenols examples include o-cresol; m-cresol; p-cresol; 2,3-dimethylphenol; 2,4-dimethylphenol; 2,3,4 trimethylphenol 3-ethyl-2,4-dimethyl-phenol; 2,3,4,5-tetramethylphenol; 4-ethyl-2,3,5,6-tetramethylphenol; 2-ethyl phenol; 3-ethylphenol; 4-ethylphenol; 2-n-propylphenol; 2-isopropylphenol; 2-isopropylphenol; 4-n-butylphenol; 4-isobutylphenol; 4-secbutylphenol; 4-t-butylphenol; 4-nonylphenol; 2-dodecylphenol; 4-dodecylphenol; 4-octadecylphenol; 2-cyclohexylphenol; 4-cyclohexylphenol; 2-allylphenol; 4-allylphenol; 2-hydroxyldiphenyl; 4-hydroxydiphenyl; 4-methyl-4'-hydroxyldiphenyl
• R and R' which may be the same or different are as defined above and m and n are integers.
• phenols include 22'-dihydroxy-55'-dimethyldiphenylmethane; 55'-dihydroxy-22'-dimethyldiphenylmethane; 44'-dihydroxy-22'-dimethyldiphenylmethane; 22'-dihydroxy-55'-dinonyldiphenylmethane; 22'-dihydroxy-55'-didodecyldiphenylmethane; 22'44'-tetra-t-butyl-33'dihydroxydiphenylmethane etc.
• R and R' which may be the same or different are as defined above, and m and n are integers and x is 1,2,3 or 4.
• phenols include: 22' dihydroxy-55' dimethyldiphenylsulphide, 55'-dihydroxy-22'-di-t-butyldiphenyldisulphide; 44'-dihydroxy-33'-di-t-butylphenyl sulphide; 22'-dihydroxy-55'-dinonyldiphenyldisulphide; 22'-dihydroxy-55'-didodecyldiphenyldisulphide; 22'-dihydroxy-55'-didodecyldiphenyltrisulphide; 22'-dihydroxy-55'-didodecyldiphenyltetrasulphide etc.
• the sulphonic acids from which the anion of the quaternary ammonium salt can be derived include alkyl and aryl sulphonic acids which may have a total of 1-200 carbon atoms per molecule although the preferred range is 10-80 atoms per molecule. Included in this description are aryl sulphonic acids of the type ##SPC7##
• n 1,2,3,4,5
• R is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl or a substituted aryl group.
• the hydrocarbon group(s) may be bonded to the benzene ring through a carbonyl group or the thio-keto group.
• the hydrocarbon group(s) may be bonded to the benzene ring through a sulphur, oxygen, or nitrogen atom.
• sulphonic acids examples include: benzene sulphonic acid; o-toluenesulphonic acid; m-toluenesulphonic acid; p-toluenesulphonic acid; 2,3-dimethyl-benzenesulphonic acid; 2,4-dimethylbenzenesulphonic acid; 2,3,4-trimethylbenzenesulphonic acid; 4-ethyl-2,3-dimethylbenzenesulphonic acid; 4-ethylbenzenesulphonic acid; 4-n-propylbenzenesulphonic acid; 4-n-butylbenzenesulphonic acid; 4-iso-butylbenzenesulphonic acid; 4-sec-butylbenzenesulphonic acid; 4-t-butylbenzenesulphonic acid; 4-nonylbenzenesulphonic acid; 2-dodecylbenzenesulphonic acid; 4-dodecylbenzenesulphonic acid; 4-cycl
• sulphonic acids of the type listed above wherein R is derived from the polymerisation of a low molecular weight olefin e.g. polypropylbenzene sulphonic acid and polyisobutylenebenzenesulphonic acid.
• R is alkyl, cycloalkyl, alkenyl or cycloalkenyl.
• sulphonic acids of this type include, methylsulphonic acid; ethylsulphonic acid; n-propylsulphonic acid; n-butylsulphonic acid; isobutylsulphonic acid; sec-butylsulphonic acid; t-butylsulphonic; nonylsulphonic acid; dodecylsulphonic acid; polypropylsulphonic acid; polyisobutylsulphonic acid; cyclohexysulphonic acid; 4-methycyclohexylsulphonic acid etc.
• the phosphosulphurised hydrocarbon from which the anion of the quaternary ammonium salt can be derived are the acids and anhydrides formed by the reaction of an olefin with phosphorus trisulphide or phosphorus pentasulphide.
• these products may be derived from propene, butene, isobutene, the pentenes, hexenes, heptenes, octenes, nonenes, decenes, dodecenes, octadecenenes etc.
• cyclic olefins such as cyclohexene, cyclopentene, cycloheptene and substituted cyclic olefins such as 3-methylcyclohexene, 4-ethylcyclohexene etc.
• the olefin may be a polymeric product derived from a C 2- C 5 olefin.
• polybutenes such as polyisobutylene, particularly when the molecular weight is in the range 500- 1500.
• the olefin may be a naturally occurring product such as a terpene or similar.
• suitable olefins include ⁇ -pinene; ⁇ -pinene, ⁇ -terpinene, ⁇ -terpinene, ⁇ -terpinene, limonene, etc.
• the quaternary ammonium salts can be made in two stages, the first stage of which comprises a tertiary amine with an olefin oxide.
• pyridine (1 mole) is reacted with an olefin oxide (1 mole) in water ( ⁇ 1 mole).
• Triethylenediamine (1 mole) is reacted with an olefin oxide (2 moles) in water ( ⁇ 2 moles).
• Hexamine (1 mole) is reacted with an olefin oxide (4 moles) in water ( ⁇ 4 moles).
• any amount of water can be used as long as it represents an excess over that required by the stoicheiometry of the reaction.
• the reaction can be carried out in the following ways:
• the amine is stirred with the olefin oxide in the reactor and the water added to the reaction mixture.
• the rate of addition of the water does not affect the quality of the final product but slow addition of water can be used to control an exothermic reaction.
• the amine is mixed with the water in the reactor and the olefin oxide is added to the stirred reaction mixture.
• the olefin oxide can be added:
• the rate of addition of the olefin oxide is not critical for the quality of the final product but a slow addition rate can be used to control an exothermic reaction.
• the olefin oxide is mixed with the water in the reactor and the amine is added to the reaction mixture.
• the amine can be added:
• slow addition of the amine can be used to control an exothermic reaction.
• the reactants when mixed are heated.
• two of the reactants can be heated together at a given temperature while the third reactant is added at a rate sufficient to maintain a steady reaction.
• the reactants can be heated in a pressure vessel and when heating the reactants to promote the reaction, temperatures greater than 100°C should be avoided to prevent decomposition of the quaternary ammonium hydroxide.
• the second stage of the reaction comprises neutralisation of the quaternary ammonium hydroxide formed in the first stage with the organic acid.
• a hydrocarbon solvent e.g. hexane, heptane, white spirit, benzene, toluene or xylene.
• the neutralisation reaction can be carried out at ambient temperature but generally an elevated temperature is used. When the reaction is complete the water and any solvents used are removed by heating and application of a vacuum.
• the product is generally diluted with mineral oil to prevent the product being too viscous.
• the quaternary ammonium salts described above are added to a lubricating oil to form a crank case lubricant.
• the lubricating oil can be any animal, vegetable or mineral oil, for example, petroleum oil fractions ranging from naphthas to spindle oil to SAE 30, 40 or 50 lubricating oil grades.
• the lubricating oil can be a synthetic oil, e.g. a synthetic ester oil.
• suitable synthetic ester oils include diesters such as dioctyl adipate, dioctyl sebacate, didecyl azelate, tridecyl adipate, didecyl succinate, didecyl glutarate and mixtures thereof.
• the synthetic ester can be a polyester such as that prepared by reacting polyhydric alcohols such as trimethylol propane and pentaerythritol with monocarboxylic acids such as butyric acid, caproic acid, caprylic acid and pelargonic acid to give the corresponding tri- and tetra- esters.
• a complex ester such as that formed by esterification reactions between a dicarboxylic acid, a glycol and an alcohol and/or a monocarboxylic acid, may be used.
• the quaternary ammonium salt is preferably included in the lubricating oil as a minor proportion by weight, e.g. 0.001 to 10.0% by weight, more preferably 0.1 to 5.0% by weight based on the weight of lubricating oil.
• the quaternary ammonium salts described are essentially ashless equivalents of metal containing additives. These additives are designed for use in lubricating oils where low ash content is desirable. Thus suitable quaternary ammonium salts may be expected to act as dispersants, detergents, antioxidants, antiwear agents, antirust additives, etc. Examples of the use of quaternary ammonium salts are given below:
• Tetramethylethylenediamine (58g 0.5 moles) was heated to reflux with propylene oxide (58g 1 mole) and water (36g 2 moles). After 30 minutes the reaction temperature reached 90°C. The reaction mixture was held at 90°C for a further 30 minutes and then the solution was added to dodecyl phenol (262g 1 mole) in toluene (150 ccs) and methanol (150 ccs). The reaction mixture was heated to reflux for 21/2 hours then the solvents removed by heating to 170°C/100mm Hg. Mineral oil (90g) was added to the residue which was then filtered through diatomaceous earth to give a bright, mobile product.
• Tetramethylethylenediamine (58g 0.5 moles), propylene oxide (58g 1 mole) and water (36g 2 moles) were heated to reflux until the reaction temperature reached 90°C.
• the reaction mixture was maintained at 90°C for 30 minutes and then added to a solution of nonylphenol sulphide (396g, effective molecular weight 792) in toluene (100 ccs) and methanol (100 ccs).
• the reaction mixture was heated to reflux for 2 hours and then the solvents and water were removed by heating to 150°C/60 mm Hg. The residue was filtered through a diatomaceous earth to give a bright, black product.
• Triethylenediamine (56g 0.5 moles) was mixed with propylene oxide (58g 1 mole) and water (36g 2 moles). There was a vigorous exothermic reaction. When the reflux subsided the reaction mixture was heated to 80°C. The reaction mixture became very viscous and water (50g) was added. Reaction mixture was maintained at 80°C for 30 minutes and then added to a solution of dodecylphenol (262 g 1 mole) in methanol (100 ccs) and toluene (100 ccs). The reaction mixture was heated to reflux for 2 hours and then the solvents and water were removed by heating to 150°C/100 mm Hg. Mineral oil (100g) was added to the product which was then filtered through diatomaceous earth.
• Hexamethylenetetramine 35g 0.25 moles was mixed with propylene oxide (58g 1 mole) and water (50g 2.78 moles). There was an exothermic reaction and the reaction mixture refluxed steadily. When the reflux subsided the reaction mixture was heated to 80°C and then added to a solution of dodecylphenol (262g 1 mole) in toluene (100 ccs) and methanol (100 ccs). The reaction mixture was heated to reflux for 11/2 hours and then the solvents and water were removed by heating to 150°C/60mm Hg. Mineral oil (85g) was added to the product which was then filtered through a diatomaceous earth to give a clear yellow, mobile product.
• TAN (D664/IP 177) 2.4 mgs.KOH/g
• Hexamethylenetetramine 35g 0.25 moles was dissolved in water (100g 5.6 moles).
• Propylene oxide 58g 1 mole was slowly added to the reaction mixture with stirring. There was an exothermic reaction and the temperature of the reaction mixture rose to 80°C but there was no reflux.
• the reaction mixture was maintained at 80°C for 30 minutes and then added to a solution of dodecylphenol (262g 1 mole) in toluene (100 ccs) and methanol (100 ccs). The reaction mixture was heated to reflux for 2 hours. Then the solvents and water were removed by heating to 150°C/100mm Hg.
• Mineral oil 88g was added to the product which was then filtered through a diatomaceous earth.
• Hexamethylenetetramine 35g 0.25 moles was stirred with water (50g 2.8 moles) and then a solution of propylene oxide (58g 1 mole) in water (100g 5.6 moles) added over a period of 1 hour.
• propylene oxide solution there was an exothermic reaction, and the temperature of the reaction mixture rose to 80°C, but the reaction mixture did not reflux.
• the reaction mixture was maintained at 80°C for 30 minutes and then added to a solution of dodecylphenol (262g 1 mole) in toluene (100 ccs) and methanol (100 ccs).
• the reaction mixture was heated to reflux for 2 hours, and then heated to 150°C/100mm Hg. to remove the solvents and water.
• Mineral oil (88g) was added to the residue which was then filtered through diatomaceous earth.
• Hexamethylenetetramine 35g 0.25 moles was dissolved in water (150g 8.35 moles) and the solution heated to 50°C.
• Propylene oxide (58g 1 mole) was added to the solution as a gas by passing a mixture of propylene oxide vapour and nitrogen through the solution.
• the reaction mixture was heated to 80°C for 30 minutes and then added to a solution of dodecylphenol (262g 1 mole) in toluene (100 ccs) and methanol (200 ccs).
• the reaction mixture was heated to reflux for 2 hours and then the solvents removed by heating to 150°C/100mm Hg.
• Mineral oil (88g) was added and the product was filtered through a diatomaceous earth.
• Propylene oxide (58g 1 mole) was dissolved in water (100g 5.6 moles). A solution of hexamethylenetetramine (35g 0.25 moles) in water (50g 2.8moles) was added slowly. An exothermic reaction took place and the temperature of the reaction mixture rose to 70°C with some reflux of the reaction mixture. When the addtion of the hexamine solution was complete the reaction mixture was heated to 80°C for 30 minutes and then added to a solution of dodecylphenol (262g 1 mole) in toluene (100 ccs) and methanol (100 ccs). Reaction mixture was heated to reflux for 2 hours and then stripped to 150°C/100 mm Hg. to remove the solvents and water. Mineral oil (88g) was added and the product filtered through a diatomaceous earth.
• Hexamethylenetetramine 70g 0.5 moles was dissolved in water (200g 11.1 moles). Propylene oxide (116g 2 moles) was added slowly over 11/2 hours. There was a mild exothermic reaction and the reaction temperature rose to 80°C without reflux. When the propylene oxide addition was complete the reaction mixture was maintained at 80°C for 30 minutes. Then dodecylphenol (524g 2 moles) was added to the reaction mixture and the temperature kept at 80°C for 1 hour. Then the temperature was raised to 150°C and the water removed from the reaction mixture by using a nitrogen sparge and vacuum (20mm Hg). Mineral oil (176g) was added to the residue which was then filtered through a diatomaceous earth.
• Hexamethylenetetramine 140g 1 mole was dissolved in water (144g 8 moles). The solution was heated to 55°C and ethylene oxide (181g 4.1 moles) was passed into the solution over 5 hours. There was an exothermic reaction and the temperature of the reaction mixture increased to 90°C. The final product was a dark, bright, viscous solution.
• Dodecylphenol (262g 1 mole) was mixed with a portion of the solution from Example 12 (115 g calculated 0.25 moles of hexamine), toluene (100 ccs) and methanol (100 ccs). The reaction mixture was heated to reflux for 2 hours and then stripped to 150°C/100 mm Hg. to remove the solvents and water. Mineral oil (85.5g) was added to the residue which was then filtered through a diatomaceous earth.
• Sulphonic acid (315g, a mixed alkylbenzenesulphonic acid of 630 MW) was mixed with a portion of the solution from Example 12 (133g) toluene (100ccs) and methanol (100 ccs). The reaction mixture was heated to reflux for 2 hours and then the solvents and water were removed by heating to 150°C/100mm Hg. Mineral oil (58g) was added to the residue which was then filtered through a diatomaceous earth.
• Hexamethylenetetramine 35g 0.25 moles was mixed with propylene oxide (116g 2 moles) and water (36g. 2 moles). The reaction mixture was heated to reflux for 71/2 hours after which the reaction temperature was 85°C. The reaction mixture was added to a sulphonic acid (350g a mixed alkylbenzenesulphonic acid of 700 MW) in toluene (100 cc) and methanol (100 cc). The reaction mixture was heated to reflux for 2 hours and then the solvents and water were removed by heating to 150°C/100mm Hg. The residue was filtered through a diatomaceous earth.
• sulphonic acid 350g a mixed alkylbenzenesulphonic acid of 700 MW
• toluene 100 cc
• methanol 100 cc
• Hexamethylenetetramine 35g 0.25 moles was mixed with styrene oxide (120g 1 mole) and water (50g 2.8 moles). The reaction mixture was heated to 50°C when an exothermic reaction took place and the temperature rose rapidly to 90°C. Reaction mixture maintained at 90°C for 4 hours and then added to a solution of dodecylphenol (262g 1 mole) in toluene (100 ccs) and methanol (100 ccs). The reaction mixture was heated to reflux for 2 hours and then stripped of the solvents and water by heating to 150°C/100mm Hg. Mineral oil (105g) was added to the residue which was then filtered through diatomaceous earth.
• TAN (D664/IP 177) 4.4 mg.KOH/g.
• An ashless multigrade oil comprised of the following:
• An oil contained the metal salt of a polyisobutylenesuccinic acid together with a conventional ashless antiwear agent, ashless antioxidant, ashless detergent and VI improver. This oil was run in the MS Vc test under standard conditions and the engine rated in the normal way. The metal salt was then replaced by a quaternary ammonium phenate (Example 6) and the test repeated. The results show that replacing the metal salt with the quaternary salt helps prevent the formation of sludge.

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• 1973
  • 1973-06-27 GB GB3050973A patent/GB1445993A/en not_active Expired
• 1974
  • 1974-06-24 US US05/482,642 patent/US3962104A/en not_active Expired - Lifetime
  • 1974-06-26 CA CA203,433A patent/CA1025428A/fr not_active Expired

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